Dichloromethane → 3-(5-Pyrimidyl)acrylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromopyrimidine (100 g), acrylic acid (48 g), triphenylphosphine (2.5 g) and palladium II acetate (0.1 g) was refluxed in tri-n-butylamine (260 ml) with overhead stirring for 4.5 h at 145-160° C. The mixture was cooled and a 10% solution of potassium carbonate (2 L) added followed by dichloromethane (500 mL). The organic layer was separated and the aqueous phase extracted with diethyl ether (3×300 ml). The aqueous layer was brought to pH 3 with concentrated hydrochloric acid (ice-cooling) and the solid so formed was filtered and dried in vacuo to give 3-(5-pyrimidyl)acrylic acid (35 g). 1H-NMR (d6-DMSO) δ 6.82(1H, d), 7.60(1H, d) and 9.15(3H, 2xs)

Provenance & Evidence